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Especially from New York and Washington, business trips to Boston
are distinctly in-and-out affairs, rarely spanning a night. The
flights are short, and the temptation to get back home is always
powerful for road warriors. Well, if you have a few days’
business in the city or are willing to allow yourself a little
time to check things out, take a look at the five essentials
below. They’ll change your view of New York’s little sister
forever.

1. Get a suite at the Colonnade: There’s no
shortage of Back Bay hotels, but the Colonnade
stands out. The friendly staff is what you’d expect in any
up-market hotel, but it’s the small touches that make the
difference. The room décor was thoughtful and tasteful, so when
you’re up working until 3 AM, you won’t be offended by an
institutional feel around you. Also, stop by Brasserie Jo in the morning for hot apple cider
(by the way, dinner there is worth your time, too).

2. Dash over for breakfast at Fill-a-Buster:
Whether your meeting is in the Back Bay or the Financial
District, make time to get over to this Beacon Hill institution.
It’s a small diner across Bowdoin Street from the capitol
building and does look as unimpressive from the outside as
within. Don’t let that deter you: Fill-a-Buster has
the best breakfast sandwiches in the city. Nobody else is even
close.

3. Meet for a cigar at Cigar Masters: I used to
hit this
cigar shop for lunch back when I worked in Boston and now
it’s a mandatory stop for me whenever I hit my ol’ stomping
grounds. It’s a great place to talk business or pleasure with
like-minded puffers, and there is a solid selection of beer and
wine on hand. Located on Boylston Street (a short walk from the
Colonnade), it is the top cigar spot in the city.

4. Wait for your flight at Santarpio’s: Before
going to Logan Airport to put Boston behind you, make some time
to get a pizza at this East Boston institution. I just went back
for the first time since leaving Boston in 2004 and was surprised
to see a (relatively) fresh coat of paint and an expanded menu
(there are actually a handful of toppings now!). The Santarpio's
grub is mind-blowing, and the staff and diners are mostly
hard-core locals. If you’re looking for a taste of Boston, this
is it. And, it’s a short cab ride up to the airport.

5. Tell the city how you feel: If the meetings
you had didn’t go as planned, use your time near the airport
(un)productively. Catch the National Car Rental shuttle, and walk out the
airport’s back exit (the driver will scream at you, but in your
mood, that won’t matter). Cross Maverick Street, and take the
Harborwalk to the end, right next to the
Hyatt. You’ll have a fabulous view of Boston that you can flip
off and hurl invectives at. Get it out of your system; you’re
about to go home.

Disclaimer: I spent two nights at the Colonnade on my last
trip to Boston free of charge and with no expectation of
coverage. My opinion is my own.